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The low vamp and padded insole made them ideal for sockless wear, especially in warmer weather

(No offense to Rory Gilmore and the students of Chilton Academy, but thats not really the vibe Im going for.) But a heel, whether its a one-inch platform or a four-inch block, helps add some shape to your leg and break up your boots silhouette

Laura Farr/AdMedia (inset) April 2007 Channeling a mermaid in a seafoam green gown with a major train at the CMT Music Awards in Nashville

And, to get started, Devil In A Blue Dress is a great place to begin

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Common Projects Minimal Runner Sneakers These are on the pricier side of the spectrum but they are truly the epitome of simple and chic